
Holiday home rentals near Chesapeake Bay
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Top-rated holiday home rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Beach/Bay Escape with Activities for All!
There's much to do from our comfortable and clean Ocean View vacation home! The beautiful Delaware beaches are a given (10 minute drive to Bethany depending on traffic.) But within a short drive there's fishing, crabbing, hiking, kayaking, golf, putt-putt and more. Just minutes to shopping, antiquing, outlet malls, and superb restaurants. Home amenities as well: large yard, game room, hammock and swings, grill, etc. The very low traffic, private road loops offer safe jogging and biking. Enjoy!

Northern Neck Waterfront
Relax with the whole family at this peaceful waterfront retreat. Nestled along Coles Creek and the Great Wicomico River, this 3-bedroom house is a perfect waterfront getaway with all the amenities you need for a comfortable stay. Savor the beauty of nature from our backyard, where a glistening pool takes center stage, inviting you to unwind and bask in the sun. If you're an aquatic enthusiast or simply someone in search of serenity, our house in Burgess offers an idyllic haven to vacation.

Designer apt with high end finishes and furnishing
Located in a large, historic townhouse in the Historic District near Lincoln Park and the Eastern Market this professionally decorated English basement apartment includes original artwork; designer furnishings chosen for comfort; and an open concept living/dining/kitchen accented by a rustic antique dining table that seats up to 6. Lush front garden with cafe' table and seating for 6. The new bathroom features double sinks, lighted medicine cabinets and an extra-large shower. Parking permit..

Cheerful 3 bedroom home with sauna
Tucked next to the Frederal civil war park in very quiet 2 acres land at a dead end street but very close to the historic Fredericksburg downtown (In 2026 summer, the pool is closed). You can take 5 minutes short walk to access the civil war park and enjoying more than 10 miles of historical beautiful federal civil war park land. Or you can just stay in the house and relax with the tranquility or the sauna. Or visit the historical Fredericksburg downtown or George Washington boyhood home.

Parkside South, Cape Charles
Parkside offers the perfect getaway for families and/or friends! Conveniently located next to Central Park, 2 blocks from the beach and the main street (Mason Ave). In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). We open corresponding weekends once the Sun-Thurs books. Check our calendar or social media for weekend openings! We recommend a max of 4 adults or 2 adults and 3 (possibly 4) children, depending on their ages. Our family of 5 stays comfortably!

Serene Cozy Couples Getaway
Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

In-Law Suite in Van Ness/Cleveland Prk/free parkin
Bright new in-law suite with a separate entrance, full kitchen, washer & dryer, fast internet, pull-out couch, laptop desks, and a pack n' play for little ones. Easy access to National Mall via Van Ness metro stop four minutes away. Flexible check in and check out, no cleaning fees (though smoking, marijuana and incense are a firm no). We've been hosting people from all over the world for several years, and we're happy to help you have a great time in Washington, for leisure or work!

Waterfront 5 Bedroom Home Close to Annapolis
Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Waterfront 4 bedroom home with marina facilities
Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

Vacay Stay-2BR/1Bath, Family Groups Only
Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Beachfront Getaway on the Chesapeake Bay!
Recharge, reconnect, and reset by staying at our waterfront home. Spend time with your crew while relaxing in this beautiful, well appointed home featuring stunning wide water views of the Chesapeake Bay. "Almost Heaven" is located at the end of a gravel lane, amongst trees, making it the perfect getaway. The expansive patio and beachfront yard offer infinity views of your private beach. Grab a glass, take a sip and put your toes in the sand!

One Bedroom Guest Studio Suite
Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.
Popular amenities for holiday home rentals near Chesapeake Bay
Family-friendly holiday home rentals

Luxurious 5 Bedroom Near Beach, Amenities Galore!

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Cozy, updated condo. Pool, tennis, walk to beach.

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Bayside Breeze in North Ocean City!

Sea Colony stunner...wooded retreat by the beach!

Private Close to Everything One-Bedroom Apartment
Holiday home rentals with a washing machine and dryer

Sara's Cottage

Spacious Garden Apartment on Delightful Street

The Observatory on Rose Manor

Down By The Bay - Cape Charles -1st Floor Primary

Relaxing 3-Bedroom Beach Cottage By Historic Lewes

Hoopers Island 4BR Waterfront • Sunset Views

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Dreams by the Sea Pool, Tennis, 2 miles to beach
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Ocean front 3 bedroom condo with pool 8/24-8/31

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Rancher central to all the fun! Fenced Yard, Deck

#3Sunset Bay homestay full kitchen with stove

Beautiful Waterfront Home

Waterfront Home with Chef's Kitchen and Firepit

New Hot Tub, Patio, Pet-Friendly-2blocks to all!

Harvest of tranquillity
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- Holiday home rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- The Mariners' Museum
- Town Point Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- USS Wisconsin (BB-64)
- Mount Trashmore Park
- Chrysler Hall





